How to Arm Yourself with the Right Questions for a Job Interview

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Every month, career coach Liz Bentley will be answering your candid questions about work, so you never have to stress about the office.


“I have an interview for a job I’m really interested in coming up. What kind of questions should I ask in the interview? And should I prep different questions if I’m meeting with multiple people?”

Standing out in an interview is—like everything else—getting harder in a world of rising competition. I often hear from my clients and friends about how they didn’t get considered for jobs where they thought they were the perfect fit. The wakeup call we are all facing is that we have to be more industrious today to achieve the same results of yesterday. Whether we want to advance in our current company or get in the door at new one, we have to show we can work hard, work smart and be able to adapt with the changing times. Asking thoughtful and provocative questions in an interview can be a game changer because it can showcase these attributes in real-time.

You are wise to go in prepared. Your questions are your chance to learn about the company and position as well as the team and managers you would be working with. The answers will help you explore what you want and need from this job. Equally important, your questions will show your potential managers and colleagues how your mind works. Here are three ways to set yourself up for success:

1. Do your homework.

Always start with Google. Research the company, the people, and the industry. This way you know the latest news, trends, issues and players. Your goal is to go in with a good understanding of their products, their market, and how they brand and present themselves. Pay attention to what they choose to emphasize about their products/services and where they dominate. You can then use this information to ask targeted questions around the opportunities and challenges facing the team/company, how the company culture drives success, or any short or long-range company plans that may change the nature of the role. When you are able to connect what you’ve learned about the company to your questions, you’ll demonstrate that you have done the work and come prepared.

You definitely should have specific questions for each person you are meeting. They should be relevant to the person’s role, provided you have that information in advance. You also should get a background on who they are so you can personalize your connection, e.g. you both like tennis, have kids, went to boarding school, have a law degree. A thorough search will likely show their career and education history, snippets from their personal life, and potentially some news stories that they may be featured or quoted in. Take note of anything relevant or interesting and ask them about it. For example, one time when I was meeting a new client, I uncovered that she had written a book called “Look Better Naked!” and my interview questions got a lot more interesting. Doing your background research will also orient you to what kind of people they like to hire. Often companies can trend toward a certain type of person based on the culture they have created.

In reviewing the industry, look for the latest trends. What are the hot topics, who are their obvious competitors, and who is winning? Get an overview of the big picture of the industry and how that relates to you and the job you are seeking. Knowing this information will help you ask the more interesting “how” questions, e.g. how will this event impact the company, how could this technological advance disrupt the industry, etc.

2. Listen and adapt.

While I think it’s really important to be prepared, the best interviewer or interviewee can turn on a dime and adapt to the dialogue at hand. That means you can really listen to the meaning of what people are saying not just the words. What are they passionate about, where are they concerned? Most interviewees make the mistake of being so focused on themselves and thinking of what they want to say next that they forget to really listen and be present. They listen to reply instead of listening to understand. Don’t make this mistake. Listen intently and draw out questions from their content. They will be impressed with your ability to connect with them, they will appreciate that you are not making it all about yourself and your questions will be much better.

This is especially crucial when talking with potential managers or team members. Pick up directly on what they are saying, whether you are discussing the attributes necessary for success, the skills the team may be missing that you could fill, the opportunities for professional development, the social side of work, or new initiatives and plans for growth. Stay with them in the discussion and have your best questions grow organically from it.

3. Personalize it, ask about them!

Be prepared and also be able to ad lib questions about the person interviewing you. To do this well, first diagnose the type of person with whom you are interviewing. Are they an externalizer (someone who talks out their thinking) or an internalizer (someone who thinks before they speak)? The externalizer will be more willing to share but also will be more likely to dominate conversation and it will be harder for you to control it. Note, you do need to have some control over the conversation so that you get your questions asked and answered within reason. The internalizer will be harder to get information out of but they will still appreciate you thinking of them. Possible questions include, “what brought you to the company,” “what do you most enjoy about working here,” and “have you had other positions.”

The goal of personalizing the questions are for you to get to know the people you may work with, understand the company culture and have a good feel for what the career path is like in this organization.

Overall, make sure you are thinking about the big picture and how these questions all come together. Remember to listen for meaning during your interview (instead of listening to reply), and be interested and interesting. Good luck!

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